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Pd-Catalyzed asymmetric allylation involving bis(diamidophosphite) based on the salen-type chiral diamine

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Abstract

New bis(diamidophosphite) ligand with stereogenic phosphorus atoms in the 1,3,2-diaza-phospholidine rings was synthesized based on (1R,2R)-[N, N′-bis(3-hydroxybenzylidene)]-1,2-diaminocyclohexane. This ligand provided up to 73% ee in Pd-catalyzed asymmetric allylic alkylation of (E)-1,3-diphenylallyl acetate with dimethyl malonate and up to 80% ee in its amination with pyrrolidine, with the starting substrate conversion being quantitative.

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Authors and Affiliations

  1. S. A. Esenin Ryazan State University, 46 ul. Svobody, 390000, Ryazan, Russian Federation

    K. N. Gavrilov, I. V. Chuchelkin, V. K. Gavrilov, S. V. Zheglov, I. D. Firsin & V. M. Trunina

  2. Moscow Institute of Physics and Technology (State University), 9 Institutskii per., 141701, Dolgoprudny, Moscow Region, Russian Federation

    A. V. Maximychev & A. M. Perepukhov

Authors
  1. K. N. Gavrilov
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  2. I. V. Chuchelkin
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  3. V. K. Gavrilov
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  4. S. V. Zheglov
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  5. I. D. Firsin
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  6. V. M. Trunina
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  7. A. V. Maximychev
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  8. A. M. Perepukhov
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Corresponding authors

Correspondence to K. N. Gavrilov or A. M. Perepukhov.

Additional information

This work was financially supported by the Russian Foundation for Basic Research (Project No. 1843623001r_mol_a).

Published in Russian in Izyestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 336–339, February, 2021.

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Gavrilov, K.N., Chuchelkin, I.V., Gavrilov, V.K. et al. Pd-Catalyzed asymmetric allylation involving bis(diamidophosphite) based on the salen-type chiral diamine. Russ Chem Bull 70, 336–339 (2021). https://doi.org/10.1007/s11172-021-3090-x

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  • DOI: https://doi.org/10.1007/s11172-021-3090-x

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